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Synthesis and Properties of Antiaromatic s-Indacene Derivatives

Research Project

Project/Area Number 21K05021
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionOsaka University

Principal Investigator

Tobe Yoshito  大阪大学, 産業科学研究所, 招へい教授 (60127264)

Co-Investigator(Kenkyū-buntansha) 家 裕隆  大阪大学, 産業科学研究所, 教授 (80362622)
Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2023: ¥130,000 (Direct Cost: ¥100,000、Indirect Cost: ¥30,000)
Fiscal Year 2022: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2021: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords反芳香族化合物 / 有機電子材料 / s-インダセン / 電子状態 / 分子構造 / 反芳香族性 / 芳香族性 / 有機半導体 / 光物性
Outline of Research at the Start

近年、光電子機能の観点から多環芳香族化合物に関する研究が精力的に行われている。一方で、反芳香族化合物は一般に不安定であるため機能材料への応用への試みは殆どなされていない。しかし、反芳香族化合物は小さなバンドギャップを有すること、高励起状態からの発光が起こりうること、さらに一重項分裂の可能性が予想されていることから、未開拓の光電子機能材料として大きな可能性をもっている。本研究では、基本的な反芳香族骨格であるにも関わらず機能面からの研究例が皆無であったs-インダセンをとりあげ、新たな合成法に基づいて多くの安定な誘導体を合成し、物性を解明することにより、反芳香族化合物の機能材料としての端緒を開く。

Outline of Final Research Achievements

To explore the possibility of optoelectronic application of antiaromatic compounds, which has been scarcely studied for that purpose compared to commonly used aromatic compounds, a new synthetic method for s-indacene derivatives bearing hexaaryl substituents bearing electron-donating or electron-accepting groups at specific positions on the indacene core was developed. By synthesizing about 30 derivatives, theire electronic strucvtures, molecular structures, and physical properties were investigated based on the quantum chemical calculations, single crystal X-ray structure analyses, and measurements of electrochemical and spectroscopic properties. A possibility for the application to organo-electronic materials was indicated by the measurements of positive carrier mobilities in organic field effect transistor devices.

Academic Significance and Societal Importance of the Research Achievements

有機電子材料は情報社会を支える先端電子機器に欠かせない基本材料であり、性能・機能の飛躍的向上のために新たな材料の発見が常に求められている。これまで用いられてきた有機物質は芳香族化合物であるのに対して、反芳香族化合物は高機能が期待されるにもかかわらず安定性に問題があるため材料への応用研究はほとんどなされていない。本課題では反芳香族のs-インダセン骨格に6個のアリール基を置換した比較的安定な化合物の合成法を開発し、その構造や基本物性を調査するとともに有機半導体への応用の可能性を調査した。本研究の成果はまだ基礎研究レベルであるが、未開拓材料の開発に貢献するものである。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • 2021 Research-status Report
  • Research Products

    (11 results)

All 2023 2022 2021 Other

All Int'l Joint Research (4 results) Journal Article (2 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 2 results,  Open Access: 1 results) Presentation (5 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results)

  • [Int'l Joint Research] National Yang Ming Chiao Tung University(その他の国・地域)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] National Yang Ming Chiao Tung University(その他の国・地域)

    • Related Report
      2022 Research-status Report
  • [Int'l Joint Research] National Yang Ming Chiao Tung University(その他の国・地域)

    • Related Report
      2021 Research-status Report
  • [Int'l Joint Research] University of New York at Albany(米国)

    • Related Report
      2021 Research-status Report
  • [Journal Article] s-Indacene Revisited: Modular Synthesis and Modulation of Structures and Molecular Orbitals of Hexaaryl Derivatives2023

    • Author(s)
      Shun-Jie Jhang, Jayabalan Pandidurai, Ching-Piao Chu, Hirokazu Miyoshi, Yuta Takahara, Masahito Miki, Hikaru Sotome, Hiroshi Miyasaka, Shreyam Chatterjee, Rumi Ozawa, Yutaka Ie, Ichiro Hisaki, Chia-Lin Tsai, Yen-Ju Cheng, Yoshito Tobe
    • Journal Title

      Journal of the American Chemical Society

      Volume: 145 Issue: 8 Pages: 4716-4729

    • DOI

      10.1021/jacs.2c13159

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Dianion and Dication of Tetracyclopentatetraphenylene as Decoupled Annulene‐within‐an‐Annulene Models2021

    • Author(s)
      Miyoshi Hirokazu、Sugiura Ryosuke、Kishi Ryohei、Spisak Sarah N.、Wei Zheng、Muranaka Atsuya、Uchiyama Masanobu、Kobayashi Nagao、Chatterjee Shreyam、Ie Yutaka、Hisaki Ichiro、Petrukhina Marina A.、Nishinaga Tohru、Nakano Masayoshi、Tobe Yoshito
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 6 Pages: 1-10

    • DOI

      10.1002/anie.202115316

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Regioselective Synthesis of Donor-Acceptor-Substituted Hexaaryl-s-indacenes2023

    • Author(s)
      Ching-Piao Chu, Shun-Jie Jhang, Jayabalan Pandidurai, Yogajivan Rout, Shreyam Chatterjee, Rumi Ozawa, Yutaka Ie, Chia-Lin Tsai, Yen-Ju Cheng, Yoshito Tobe
    • Organizer
      The 15th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 1,2,3,5,6,7-Hexaaryl-s-indacenes: Concise Synthetic Approach to Specific Donor or Acceptor Substitution Patterns2022

    • Author(s)
      Shun-Jie Jhang, Jayabalan Pandidurai, Ching-Piao Chu, Hirokazu Miyoshi, Yuta Takahara, Masahito Miki, Shreyam Chatterjee, Yutaka Ie, Yen-Ju Cheng, Yoshito Tobe
    • Organizer
      19th International Symposium on Novel Aromatic Compounds
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] Generation and Self-Aggregation of Tetraanion of Tetracyclopentatetraphenylene2022

    • Author(s)
      Hirokazu Miyoshi, Yusuke Kurogi, Rumi Ozawa, Shreyam Chatterjee, Yutaka Ie, Yoshito Tobe
    • Organizer
      19th International Symposium on Novel Aromatic Compounds
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] s-Indacene Revisited: Modular Synthesis of Hexaaryl Derivatives2022

    • Author(s)
      Shun-Jie Jhang, Jayabalan Pandidurai, Chin-Piao Chu, Hirokazu Miyoshi, Yuta Takahara, Masahito Miki, Yen-Ju Cheng, Yoshito Tobe
    • Organizer
      The 15th International Symposium on Organic Reactions
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 反芳香族化合物:再考2022

    • Author(s)
      戸部義人
    • Organizer
      有機合成化学協会中国四国支部特別招待講演会
    • Related Report
      2022 Research-status Report
    • Invited

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Published: 2021-04-28   Modified: 2025-01-30  

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